A New Challenge
by SakuraLeaf
Summary: Ash has just won the Kalos league and heads back home, but a single unexpected confession keeps him unable to celebrate his newest victory. Will Ash finally think about something besides Pokemon? Expect a pokeshippy ending.
1. Her Last Chance

*****Edit 1/15/2014*****

Okay so it's come to my attention that I haven't made the summary clear. Sorry about that! To make things clear, **this story will have a Pokeshippy ending. **

**Summary: **Ash is confused about the whole "liking someone" concept so he first thinks he likes Serena, but in the end realizes that he actually already liked someone and just didn't know it.

*****Author's Note*****

Hello readers! This is my first story :) To make things less confusing, thoughts are in italics. Also, each chapter focuses on different character's thoughts. This one focuses on Serena's thoughts. Thanks for reading and I hope you enjoy! I like the way I wrote chapter 2 way better than this one so if it seems choppy don't give up just yet!

**Disclaimer: I don't own Pokemon.**

**A New Challenge  
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Chapter 1: Her Last Chance

Serena had been working up the nerve to finally admit her crush on Ash. But she didn't know how. Everytime she finally gained the courage to do so, she backed out last minute. But maybe this time she would finally be able to go through with it.

_He won the league! I'm so proud of him. I always knew he could do it. _

She silently stared at him while he was busy enjoying his win. Clemont and Bonnie were by his side, also very proud of their friend's achievement. But Bonnie noticed Serena hadn't said anything to Ash yet.

"Serena! Come! Join us! Aren't you going to congratulate Ash for winning?!" Bonnie asked while she reached out to grab Serena's hand. Serena didn't even have the chance to respond as she was being pulled away by her little friend. "Ok!" was all she could say.

"Serena!" Ash had a big smile on his face.

"Congratulations Ash! I always knew you could do it." She blushed slightly.

"Thanks! Everyone let's go celebrate...with food!"

"Pika!"

And with that the four friends left towards the nearest restaurant they could find.

_Should I tell him? He seems so happy right now, I don't want to ruin his big win. But...but if I don't tell him I don't think he'll ever get the idea. Why does he have to be so dense?! But then again...that is what I like about him. He's so sweet and he doesn't even know it. _

Everyone but Serena was busy laughing and talking about the battle on their way to celebrate.

"Ash! You have to teach me those techniques!"

"Well you're not so bad yourself!"

"I'd like to try winning the league myself. Ash, I never told you but you've inspired me to beome a better trainer. I think I really will try to win the league myself. Of course, with science by my side that is!"

"Serena, what about you? What do you plan to do?"

Serena was caught off guard. She hadn't been listening to the boys conversation and therefore had no idea what Ash had just asked her.

"Yeah Serena, what do you want to do?"

Luckily for her, Clemont had repeated Ash's question.

_What do I want to do? Oh they must be asking about what I plan to do next. _

_I want to travel. I love the idea of exploring the world. It's just...just so exciting! When I was little I didn't really like the idea of leaving home, which is why my parents tried their best to show me what the world has to offer. That's actually why I ended up going to the Pokemon camp in Kanto. My parents decided it would be a great opportunity for me. I was so scared. I hated being there, well at least until I met Ash. He made me feel so safe. He wasn't afraid. After that encounter, I began to open up to the world a bit more. I was still scared, but I thought that if Ash could do it so could I. Years passed and I came to the conclusion that maybe it wouldn't be so bad to travel. That's when I found out Ash was in Kalos. Any doubt that I had about starting my own adventure soon diminished and I was finally ready to leave the comfort of my home._

"Serena?" Bonnie looked at the girl with confusion.

"Huh? Oh! Sorry, I was just thinking about something." Serena was flustered but soon found her composure and continued to speak, "To answer your question Ash, I still don't know exactly what I want to do, but it doesn't matter. I'd like to continue to travel. Maybe I'll find out what I want to do in the process!"

"I'm glad for you Serena. I hope that traveling with us has been fun!"

_Traveling with you, Clemont and Bonnie has been fun! I've learned so much and have been able to find the joy and excitement of traveling. Maybe I'll want to win the league myself one day! I'm getting ahead of myself. But hey, maybe I will. _

_Hmm..Why had he asked me to join them back then? _

"It was! I've learned a lot about pokemon and about myself. Thank you."

"For what?" Ash looked confused.

"Well, if you hadn't asked me to join you on your journey, I may have given up by now."

Ash didn't look so confused anymore. He smiled and continued to say, "I'm glad I asked then! But you should also give yourself more credit. I'm pretty sure that no matter who you traveled with or where you traveled, you would have been able to continue your journey."

Serena gave a slight smile and a slight blush.

_Thank you Ash. _

"But I'm glad it was with us!" Bonnie was quick to add. Over the course of their travels, Serena had come to see Bonnie as her own little sister. Their bond was quite strong.

"Yeah, it was fun traveling with you! I'm just sorry you had to see all of my experiments fail. But never give up on Science!" Clemont laughed nervously as he scratched the back of his head.

There was a moment of silence until Ash decided to break it, "So are you guys going to continue to travel together?" He directed his question at his three friends, who all looked so puzzled. Until it hit them.

_Ash won't be traveling with us anymore? I knew this day would come, but I didn't think it would happen anytime soon. _

"You mean you won't be traveling with us anymore?" Clemont had become good friends with Ash, it made him feel sad that his dear friend wouldn't be traveling with him anymore.

"I've had fun on this journey and I'm glad we all became good friends! But after winning this league I need some time to go back home and start thinking about my next adventure!" Ash had that reassuring smile he has whenever he tries to cheer his friends up. He knew that leaving them would hurt them as much as it hurt him. Even though he has gotten better at it, Ash has always had a hard time saying goodbye.

_He can't leave. I don't want him to leave. But I know that no one will nor can stop him. Not even me. And I won't try. Even if I could, I would never be the one to stop him from continuing his dream. Especially since he was the one who has taught me to never give up. So I guess this is goodbye. But...before he leaves..._

"Ash..."

"Yes, Serena?"

"Take care! I wish you luck on your journey!"

"Yes, take care and good luck!" Clemont and Bonnie added in unision.

"Same! Bonnie make sure to take care of your brother! And Clemont...make sure you win that league!" Ash had an even bigger smile this time. "Serena! Don't forget to tell me what your dream is when you find it!"

"Pika Pika!" The yellow rodent could not be left out of this farewell.

With his last farewells, the skilled young trainer made his way towards the door and was soon on the road to the airport.

_Well...he's gone and I didn't get to tell him. If Bonnie and Clemont weren't there, maybe it would have been easier. Hey! _

"Bonnie. Clemont. I have to go somewhere real quick, will you guys wait for me here?"

"So you aren't also leaving us?!" Bonnie was relieved. With Ash's farewell, Bonnie was afraid that Serena would be the next to leave.

"I still have some traveling to do! But I have one thing that I need to take care of first."

*****Author's Note*****

If you've made it through, please leave a review ;)


	2. Confession Confusion

*****Author's Note*****

Hello again readers! Thank you for reading :) This one focuses on Ash's thoughts (in italics).

**Disclaimer: I don't own Pokemon.**

**A New Challenge  
><strong>

Chapter 2: Confession Confusion

"Ash!"

_I thought I just heard someone yelling my name._

Ash was slowly walking under the night sky with the pebbled floor reflecting the moon's light. He wasn't thinking much about anything. He was tired, but the mention of his name made him aware of his surroudings.

"Pikapi?" Pikachu tried to find where the voice was coming from.

"Ash...Ash hold on a second." Serena was trying to catch her breath.

_Serena?_

"Ah! Serena!"

"I'm glad I was able to catch up with you! I thought you might have already been at the airport by now."

"Well, I'm a bit tired so I was taking my time" Ash laughed embarrased while holding the back of his head with his hand.

Serena decided to sit down on a nearby bench and Ash did the same.

"So why did you want to catch up with me?"

"There's something I forgot to tell you before..." Serena was battling with herself but eventually decided that it was now or never, "actually, this is something I've been meaning to tell you for a while now. But I just don't know how to."

Ash gave that reassuring smile once again.

"Don't worry. If you don't know how to say it, then- "

"I don't want you to leave! I want to keep traveling with you! I don't want you to leave because I...because I...I'll miss you. I'll miss you a lot."

Serena was trying to read Ash's face, but she didn't find the face she was looking for.

"I'll miss you too Serena, you and Clemont and Bonnie." Ash still had that reassuring smile of his.

"You don't understand do you?"

_I don't understand? What don't I understand?_

"I like you. I always have. And not just as a friend...I like you much more than that"

Serena made sure that her eyes didn't meet his.

_Oh. That's what I don't understand. Wait?! She likes me?! What- What am I supposed to say? Man, I hope she says something because I sure don't know what to say._

"Uh...Umm..."

"You don't have to say anything"

_Phew_

"I just wanted to let you know. I'm not expecting you to say anything, let alone feel anything for me. I just wanted to let you know."

_Serena is not the first to tell me she likes me, but she is the first to sound upset about it. Maybe I should say something. But what can I say? _

"It's okay."

She looked up at him with hope in her eyes.

_Uh...why is she looking at me like that? Maybe I should say something else._

"I think it's okay if you like me."

Serena tried to read his face once more, but once again, did not find the face she was looking for.

"Have you ever felt something special for someone?"

_What? Why is she asking me this? I think I can live with her liking me, but why are we now talking about my feelings?_

"I uh...I don't think so."

"I see."

_Why does she sound so sad? Wait...maybe she wanted to know if I liked her. But I don't know what it feels like to like someone. How am I supposed to know if I feel that way for her?_

"Um..how does it feel like?" He asked with a blush slowly appearing on his face.

"Huh?"

"I don't know what if feels like to like someone...so I can't say whether or not I ever did or did not like someone." Ash's blush was becoming more red.

"Oh, I see" Serena gave a small giggle. She was now certain that her crush didn't feel the same way for her, but she didn't mind so much. She was so amused with his cuteness, that she didn't mind if he felt the same way so long as she could continue being his friend.

"Well there are many ways to figure it out. You know you like someone if whenever you see him or her you start to feel nervous."

_Feel nervous? Wait, this doesn't make sense. If I always feel nervous around Gary, does that mean I like Gary? That can't be right, can it? _

Seeing the confused look on his face, Serena decided to try a different tactic.

"Hmmm...Ash have you ever looked at someone and thought he or she was handsome or beautiful?"

"Yeah. My mom, and most of my friends are quite beautiful."

"Is there anyone that you like looking at?"

_Like looking at? Oh she's probably asking if I have looked at someone and thought they were pretty like Brock does with any pretty girl he sees. But I think a lot of people are pretty. Does that mean I like that many people? That doesn't make sense either._

Finally, Serena decided to stop trying to explain the concept of love to the trainer. Instead she just described what she feels for him.

"Ash...you know you like someone if when you see them you feel happy. An immense happy that you wish would never fade away. Not the kind of happy you feel when you win a match, but the kind of happy that makes you feel warm inside. You know you like someone if when you are far away from them you feel sad. Not the kind of sadness you feel when you lose a match, but the kind of sadness that makes you feel empty inside. A sadness that won't go away unless you are with that person. You know you like someone if you keep thinking about that person and don't want to stop."

_No, I don't think I have ever felt this way for anyone._

"I understand. Is there anything I can do, I can say to make you feel better?"

"I'm okay Ash. I just had to tell you what I felt before you go. Now I know how you feel about me, and I can't do anything more than continue being your friend."

"You know...I really don't mind it if you like me. I mean, you can't choose who to like, right? I hope you are able to find happiness and maybe you'll find it while travelling with Clemont and Bonnie!" Ash gave Serena that reassuring smile of his one last time. And for the first and last time, she gave him her own reassuring smile.

"Thank you. I have to get back to Clemont and Bonnie! I wish you luck with everything!"

And with that last sentence the two parted ways, Serena felt calm now. But now it was Ash's turn to feel nervous and confused.

*****Author's Note*****

If you've made it through, please leave a review ;)


	3. Serena?

*****Author's Note*****

Thank you for reading! This chapter also focuses on Ash's thoughts.

**Disclaimer: I don't own Pokemon.**

**A New Challenge  
><strong>

Chapter 3: Serena?

Ash hadn't ever thought about what it meant to like someone. He just lived for battles and his pokemon. He cared for all his friends deeply. He had never once considered he might like any of them. But now that one of his own friends had confessed to him, he couldn't let the thought escape his mind. All the way home he kept thinking about Serena's words. Each and every single one.

_Serena likes me? This doesn't make any sense. Ugh! I am always ready to accept a challenge, but the kind of challenges that involve Pokemon not...not...not this! Why is this bothering me so much? Why did I tell her it was okay?! It's not okay. I'm not okay. _

Once home though, Ash buried his thoughts deep in his mind.

"Pikachu! We're home buddy!" Ash and his small friend admired the town of Pallet from the edge of a cliff. It was a rather sunny day and the town was shrouded with the green trees of Summer.

_It's good to be back. _

Back in Pallet, Delia was more than excited at the thought of her son coming back from his journey. She wondered if he was coming back alone or with friends. Delia loved meeting all of Ash's friends, so much so that she decided to invite all of Ash's friends to welcome him with her.

"Hi Ash! Welcome home."

"Hi mom!"

"Pika!"

"Congratulations Ash!" Misty, Brock, Duplica, Ritchie, May, Max and Dawn all cheered in unison.

"Uh, uh thanks guys! What are all you guys doing here?"

"Congratulations Ashy boy, I had some doubt but you proved me wrong and won anyway."

"Gary!"

"The one and only."

"My grandson is right Ash, you've had your share of obstacles to overcome but you always come through in the end."

Ash, feeling abashed at the attention, stood there in front of his friends and family not knowing what to say next. However, he did manage to say one thing, "Everyone...let's eat!" and with that the house was filled with laughter.

_Why is everyone laughing? _

In the backyard the welcome party was set up with streamers and a homemade 'Congratulations Ash!' sign. Ash's pokemon were out and about mingling with other pokemon, pikachu included.

"Hey Ash, it's been a long time huh? How has traveling around Kalos been? Still being sidetracked by Team Rocket?" Misty giggled and gave a wink with her last question.

"Yeah Ash, how was Kalos? I bet you there were lots of pretty girls there..." and with that Brock was in a trance.

Suddenly Ash's mind went to Serena.

"I..uh.." Ash was flustered and a light blush appeared as he turned his eyes away from Brock and towards the ground.

_Serena? _

"What's wrong Ash?" Misty was usually able to read Ash's face, but this was not one of those times.

Hearing the sound of Misty's voice, Ash came back from his thoughts and answered, "What? Oh. Nothing's wrong."

"When someone says nothing is wrong it usually means something is wrong. Now fess up!"

"Uh, uh...I don't even know what's wrong."

"What do you mean?"

_Misty, could you please just spare me this time? Please. _

"It's just-" BOOM!

"What was that?!" A startled Brock, who was finally awake from his trance due to the explosion, tried searching for the origin of the boom.

"It's Team Rocket!"

For the first time in his life, Ash was glad to see Team Rocket.

*****Author's Note*****

If you've made it through, please leave a review ;)

This is all I have for now, but if people want to keep reading I'll soon get to writing chapter 4!


	4. Two Idiots

*****Author's Note*****

Ah! I can't believe it took me so long to update :( I had it done, but I have a bad habit of editing more than I need to. So now this is the final product. I hope you guys like it. It was hard for me to write in Team Rocket, but I hope it's decent. Also I wanted to call this chapter Reflections and Suspicions but after I edited it I changed my mind. I hope Misty is not too out of character. One last thing, I noticed it's mainly dialogue towards the end, tell me what you think about that. Should I add in more descriptors? Okay I'm done, enjoy :)

**Disclaimer: I don't own Pokemon. Seriously, I don't.  
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**A New Challenge  
><strong>

Chapter 4: Two Idiots

"Team Rocket! What are you doing here?! Can't you just leave us alone? You can come back tomorrow."

"Well if it isn't the twerpette, annoying as ever."

Over the years Misty had learned to control her temper, but her reunion with Team Rocket had proven to be a bit too provoking.

"You better leave now you old hag!"

As Meowth tried to hold a fuming Jessie back, James took the opportunity to speak, "We're just here to congratulate the twerp. If we're going to be losers then we should at least lose to a worthy opponent."

_Of course. Only Team Rocket would say such a thing. Wait...then...why the explosion?_

"Wait a minute. What about the explosion?"

"We wanted to make an explosive entrance."

With her hand covering her face, Misty fought the urge to say anything else. Was there anything else she _could_ say?

"Thank you for coming Jessie, James and Meowth. You guys may go over to the snack table and make yourself comfortable!" Delia always knew that the trio cared for her son, in a very peculiar way, but Delia was never to turn down someone who had even the slightest of a caring relationship with her son.

"Are you sure we can let them stay ?" Misty was still not convinced.

"Of course I am! You should probably go find Ash!"

_Where did Ash run off to? Why didn't he try to stop Team Rocket...that's right! I was about to get him to fess up when Team Rocket decided to drop in. What's going on with him? Something _must _be wrong. No...something _is _wrong._

"Ash Ketchum! I found you. Don't you think you can get away with this!"

Misty's stern words where accompanied by finger pointing.

"I uh...um what do you mean?" Ash questioned while trying to feign ignorance. Normally, Misty would let it go as she knew just how dense Ash could be. But his nervousness gave it away.

_I just don't get it. Why would Ash try to hide what was going on with him? What's worse, I think I lost the ability to read him. Ash Ketchum, you better have a good reason to not tell me._

Knowing he was not going to win Ash decided to give up, but all of a sudden, "Ash! Misty! There you are. I've been looking for the two of you."

"Brock!" The two replied in unison.

_Great! Maybe I can get Brock to help me._

"Brock, something is wrong with Ash but he doesn't want to say anything about it. You'll help me right?"

Brock was always quick to help his friends, but this time he wasn't so sure. He didn't think there was anything wrong with Ash. In the end, Misty's plea's won him over.

"Alright. Ash what's wrong with you? You know...I don't know why Misty would think there is something wrong with you. But if there is something wrong, you know you can count on us. We're your best friends."

Ash eyed Brock in hopes of communicating a call for help, but Misty kept at it, "Ash! I can see you, you know?"

"Misty! I know I said there was something bothering me, but it's no big deal. I mean it."

"Wait, so there is something wrong with you?"

Ignoring Brock's inquiry Ash continued, "I know you're worried about me, but I'll figure this out on my own."

"Fine! If you think you can do this on your own, then be my guest. But I doubt you'll figure it out, whatever it is, with that brain of yours! Hmph!" And with that, Misty left a hurt Ash with a confused Brock.

"Ash, she was just trying to help you know?"

"I know, but...how can I...tell her about something I'm not even sure about myself?"

"What do you mean?" If Brock wasn't intrigued before, he now was.

"Aw come on! Not you too Brock! You guys really think I can't figure this out on my own?"

"Not really. But that's why we're here to help you. Although unlike Misty, I think it's best if we just wait until you're ready."

"Thanks Brock. I knew you'd understand."

"I'm going to go check on Misty for a while. I hope you come to us when you're ready."

_That jerk! I was just trying to help him! Why does he have to be so stubborn? If he'd just let me help him...maybe I could...maybe he would...be happier. He said it was no big deal, but if it wasn't such a big deal then he would tell us. He said he doesn't even know what's wrong and that's probably hurting him more than what _is_ wrong. _

_I've finally been able to see him again after all this time, and now he doesn't even trust me? And now he probably thinks I hate him. This is the first time we've seen each other since traveling with Brock, May and Max and all I've done is terrorize him. Why am I so selfish? If he doesn't want my help, then I probably shouldn't help him. Right? _

"Misty! Misty!"

"Huh?"

"Misty!"

"Oh hey Brock."

"First something was wrong with Ash and now I think something is wrong with you. If you're worried about Ash, don't be. He'll open up to us when he's ready."

"But that's exactly why I'm worried. What's taking him so long? Why won't he tell us anything? At first I didn't think it was a big deal either, but the fact that he isn't telling us anything is not right. Not if it's Ash we're talking about."

"You're right. This isn't like Ash, but trying force it out of him won't get us anywhere. The only thing we can do is wait. But I do have a question for you."

"What is it?" Misty was quite curious to know what Brock wanted to ask her. She had been doing most of the questioning for most of the party's duration.

"What made you think something was wrong with him in the first place?"

_Hmm...he's right! Ash had that face...that face I was unable to read. What could it mean? _

"Misty?"

"Oh right! When you were talking to Ash about Kalos, and then tuned out as usual, Ash had a weird expression on his face. I can usually tell what's going on with him, but now I just can't. I guess we're just not as close anymore..." Misty's aqua green eyes began to slowly form tears. But she made sure those tears never made it past her eyes.

"Misty...Ash cares about you and you know that. Just because you can't understand him as well as you used to it doesn't mean you're a bad friend."

Brock put one comforting hand on Misty's shoulders and said, "Now go on and be happy for that idiot friend of yours! If he's not worrying, then you shouldn't either."

"That's right! The party! I can't believe I'm here worrying for that idiot of a friend. Ash Ketchum, you better not be having a good time without me!"

_Yes Ash is an idiot, but he's the idiot that I...that I care about._

As Brock watched Misty move towards the crowd, a small gentle smile formed on his face, "I guess I must also be an idiot for calling those two idiots my best friends."

*****Author's Note*****

So there you have it! I'm sorry if it wasn't what you were expecting. I made a lot of changes, though the overarching plot is still working out the way I had planned it :) I have the main ideas for chapters 5 - 8 and even their titles, but that might change slightly until I actually write the chapters. I'm hoping it'll only take me 2-3 weeks to update. And yeah please review, I read them all :)


	5. How it would have played out

**Update 7/12/2014**

I will no longer be using this account and as a result will not be updating A New Challenge anymore. I have included this fifth chapter explaining in detail how I would have liked the story to play out. I apologize to anyone who was expecting an update.

**How it would have happened:**

Ash would have eventually consulted Misty about his mixed feelings for Serena. Misty is heartbroken but decides to help Ash anyway. Misty and Ash come up with several "confession" plans, but Ash manages to ruin them every time. Misty, being hotheaded, ends up calling out Ash for his failures. Every time Ash fails, he gains insight on his feelings for Misty. His last and final "failure" occurs when he ends up confessing his feelings for Misty to Serena. Serena isn't heartbroken because she knew ever since chapter 2 that he didn't feel anything for her. Roles get switched. Serena helps Ash confess to Misty. Unlike with Misty's plans, Ash does not fail Serena's plan. He wins the challenge.


End file.
